Cadaverine → HCID 178512165, compound

HRID 2258158Notes

Reaction equation

HRID 2258158 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12](=[NH:16])OCC)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH2:23]>C1(C)C=CC=CC=1>[NH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:12]([NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])=[NH:16]

Participants

4

Reactant 2

HCID 273CadaverineHCID 145824581benzyl N-(C-ethoxycarbonimidoyl)carbamate

Product 1

HCID 178512165HCID 178512165, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of N-benzyloxycarbonyl-O-methyl-isourea (II-OMe) (0.42 g, 2.0 mmol), toluene (3.5 mL) and 1,5-diaminopentane (0.50, 5.0 mmol) was stirred at 40° C. and for 48 h. The reaction mixture was concentrated under vacuum (35° C., 0.3 mbar) to give a crude product which was crystallized by addition of toluene followed by additon of heptane. The yield of N-(5-aminopentyl)-N'-benzyloxycarbonyl guanidine (IIId) was 0.3 g (60% in theory).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum (35° C., 0.3 mbar)

Sources & evidence

ORD record
ord-d3bf2018e0004dd1bd87b8542f0f392a
Source dataset
uspto-grants-1997_08
Patent number
US05659071

Reaction notes

Loading…